6-[1-Phenyl-2-(imidazol-1-yl)ethenyl]-3,4-dihydrocarbostyril → 6-[1-Phenyl-2-(imidazol-1-yl)ethyl]3,4-dihydrocarbostyril

HRID 414561Notes

Reaction equation

HRID 414561 reaction equation
[C:1]1([C:7]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[CH2:18][CH2:17]3)=[CH:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)C.[Pd]>[C:1]1([CH:7]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[CH2:18][CH2:17]3)[CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 536619046-[1-Phenyl-2-(imidazol-1-yl)ethenyl]-3,4-dihydrocarbostyrilHCID 178418361HCID 178418361, compound

Product 1

HCID 143732756-[1-Phenyl-2-(imidazol-1-yl)ethyl]3,4-dihydrocarbostyril

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 390 mg of a mixture of (E) and (Z) isomers of 6-[1-phenyl-2-(imidazol-1-yl)ethenyl]-3,4-dihydrocarbostyril in 10 ml of ethanol was stirred under hydrogen in the presence of 200 mg of a 10% palladium on charcoal catalyst until the theoretical amount of hydrogen had been absorbed. The catalyst was filtered off, the solvent removed from the filtrate under reduced pressure and the residue chromatographed on silica gel eluting with 5% methanol in methylene chloride, yielding 6-[1-phenyl-2-(imidazol-1-yl)ethyl]3,4-dihydrocarbostyril, having a melting point of 87°-94° C.

Workup

  1. customhad been absorbed
  2. filtrationThe catalyst was filtered off
  3. customthe solvent removed from the filtrate under reduced pressure
  4. customthe residue chromatographed on silica gel eluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-aef1b0d9750d42118707f36dcb32ad3b
Source dataset
uspto-grants-1988_12
Patent number
US04792561

Reaction notes

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